Details of the Drug

General Information of Drug (ID: DMI5OXG)

Drug Name

Latanoprost

Synonyms

Catioprost; Xalatan; Latanoprost free acid; L1167_SIGMA; PhXA41; XA41; AR-202; Nova-21027; PHXA-41; XA-41; Xalatan (TN); Latanoprost (JAN/USAN/INN); PhXA34 [as 15(R,S)-isomer]; Isopropyl (5Z,9alpha,11alpha,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinorprost-5-en-1-oate; Isopropyl (5Z,9alpha,11alpha,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate; Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate; Propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; Propan-2-yl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate

Indication

Disease Entry	ICD 11	Status	REF
Ocular hypertension	9C61.01	Approved	[1]
Open-angle glaucoma	9C61	Approved	[2]
OPTN-related open angle glaucoma	N.A.	Approved	[1]
Glaucoma/ocular hypertension	9C61	Phase 2	[3]
Ocular disease	1F00.1Z	Investigative	[4]
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Therapeutic Class

Antihypertensive Agents

Affected Organisms

Humans and other mammals

ATC Code

S01EE01: Latanoprost

S01EE: Prostaglandin analogues

S01E: ANTIGLAUCOMA PREPARATIONS AND MIOTICS

S01: OPHTHALMOLOGICALS

S: SENSORY ORGANS

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

432.6

Logarithm of the Partition Coefficient (xlogp)

4.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 53 ng/L [5]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 5 min [5]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [6]
Clearance: The sytemic clearance of drug is 7 mL/min/kg [7]
Elimination: About 88% of the latanoprost dose is recovered in the urine after topical administration [8]
Half-life: The concentration or amount of drug in body reduced by one-half in 17 minutes (from the plasma), and 2C3 hours (from the eye) [9]
Metabolism: The drug is metabolized via the esterases to become a pharmacologically active drug [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.1% [10]
Vd: The volume of distribution (Vd) of drug is 0.16 +/- 0.02 L/kg [7]
Water Solubility: The ability of drug to dissolve in water is measured as 0.05 mg/mL [6]

Chemical Identifiers

Formula: C26H40O5
IUPAC Name: propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
Canonical SMILES: CC(C)OC(=O)CCC/C=C\\C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O
InChI: InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1
InChIKey: GGXICVAJURFBLW-CEYXHVGTSA-N

Cross-matching ID

PubChem CID: 5311221
ChEBI ID: CHEBI:6384
CAS Number: 130209-82-4
UNII: 6Z5B6HVF6O
DrugBank ID: DB00654
TTD ID: D0C6NM
VARIDT ID: DR00168
ACDINA ID: D01199

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Prostaglandin F2-alpha receptor (PTGFR)	TTT2ZAR	PF2R_HUMAN	Agonist	[11]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic anion transporting polypeptide 2A1 (SLCO2A1)	DT021JD	SO2A1_HUMAN	Substrate	[12]
Organic anion transporting polypeptide 2B1 (SLCO2B1)	DTPFTEQ	SO2B1_HUMAN	Substrate	[12]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[13]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Ocular hypertension

ICD Disease Classification

9C61.01

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Prostaglandin F2-alpha receptor (PTGFR)	DTT	PTGFR	8.25E-02	-0.05	-0.14
Organic anion transporting polypeptide 2B1 (SLCO2B1)	DTP	OATP2B1	6.30E-05	2.52E-01	5.88E-01
Organic anion transporting polypeptide 2A1 (SLCO2A1)	DTP	OATP2A1	3.03E-03	-9.85E-02	-3.19E-01

Molecular Expression Atlas (MEA)

MEA Detail

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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Hydrochloric acid	E00015	313	Acidulant
Ricinoleic acid	E00442	643684	Emollient; Emulsifying agent
Disodium hydrogenorthophosphate	E00283	24203	Buffering agent; Complexing agent
Edetate disodium	E00186	8759	Complexing agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Sodium chloride	E00077	5234	Diluent; Tonicity agent
Sodium hydroxide	E00234	14798	Alkalizing agent
Sodium phosphate monobasic monohydrate	E00428	516949	Buffering agent; Complexing agent
Water	E00035	962	Solvent
Boric acid	E00152	7628	Antimicrobial preservative; Buffering agent
Sodium borate	E00511	11954323	Alkalizing agent; Antimicrobial preservative; Buffering agent; Emulsifying agent
Polyoxyl 15 hydroxystearate	E00659	Not Available	Emulsifying agent; Solubilizing agent; Surfactant
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Latanoprost 0.005% solution	0.01%	Solution	Ophthalmic

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Latanoprost FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1961).
3	Clinical pipeline report, company report or official report of Mati therapeutics.
4	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 344).
5	Sunehag A, Tigas S, Haymond MW: Contribution of plasma galactose and glucose to milk lactose synthesis during galactose ingestion. J Clin Endocrinol Metab. 2003 Jan;88(1):225-9. doi: 10.1210/jc.2002-020768.
6	BDDCS applied to over 900 drugs
7	Xalatan FDA label
8	Sandoz Latanoprost monograph
9	Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014.
10	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
11	PGF(2alpha) FP receptor contributes to brain damage following transient focal brain ischemia. Neurotox Res. 2009 Jan;15(1):62-70.
12	The prostaglandin transporter OATP2A1 is expressed in human ocular tissues and transports the antiglaucoma prostanoid latanoprost. Invest Ophthalmol Vis Sci. 2010 May;51(5):2504-11.
13	A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov;136(1):216-41.